Roy Dickerson and the Stoner Train Robbery of 1889

Roy was widely known as one of the best cowboys in the Four Corners states. He was born in 1879 and died here in 1955. His grave is at the Peoples Cemetery near Dolores. He would stay with us at our ranch in Thompson Park in the summer and in Kingman, Arizona, with Leonard Neal in the winter after he no longer was “working for the brand.” Roy would often tell my dad and me stories of the early days in Southwest Colorado. One of my favorites was his encounter with desperadoes when he was 10 years old.

Roy and his cousins, the Millard boys, were helping Mr. Millard brand cattle. After the branding was finished and cattle turned out, the boys were playing around the corrals. These corrals were near Stoner and close to the place where the railroad had a water tower.

A man on horseback rode up and started a conversation with the boys.

The boys thought it peculiar that the man was bareheaded, as cowboys always wore hats in those days.

He asked them several questions about the train, such as when the train would be stopping for water. They told him that the train was expected at noon that day. The man continued to sit on his horse and small talk with the boys. He looked up at the sun and asked the boys what time that they thought it was. They replied that is was around noon. The man said, “You boys had better get the hell out of here because there is going to be some bad things happen pretty soon.” That, of course, only piqued their curiosity. The boys hid in some willows that were close to the water tower.

Several other men rode up horseback to wait for the train’s arrival. As soon as the train stopped, the outlaws made everyone on the train get off. The passengers and crew were held at gunpoint.

The outlaws took out several gunnysacks and had every man on the train put his hat into the sacks.

The robbers also helped themselves to other valuables from the passengers and the cargo. After getting their loot, the outlaws rode by the willows where the boys had hidden. As they rode by, the bareheaded waved in their direction and said, “So long, boys.”

My great-uncle Carroll Pyle was on the train that day, as was Walter Wallace. It seems that Walter had had terrible luck on his trip to Denver. He had a hat stolen on the trip up. He bought a new one in Denver, which was stolen at his hotel. He acquired yet another hat before returning to Dolores and lost that one to the outlaws. Walter was so upset when he got to Dolores that day he said that, “The next person who tries to take my hat is going to have to kill me first because I won’t be giving up another one.”

The outlaws who robbed the train that day were later identified as Butch Cassidy and the Wild Bunch. Seems that they had robbed the Bank in Telluride the day before. While making their getaway, Butch Cassidy was riding a half-broke horse. As they were leaving Telluride, the horse started to buck and was hard to ride, causing Butch to lose his hat and almost his seat. He was in too big of a hurry to retrieve his hat. Butch Cassidy was the bareheaded man who met with Roy and his cousins at the water tower near Stoner that day.

About the Pyles

The Pyle families were very early settlers of the “Big Bend on the Dolores River.” The families moved to the new Town of Dolores when the railroad came into the area. Prior to that time, the railroad ran from Ridgway to Durango, Colorado (per research).

Frank Pyle is a past chairman of the Board of Directors of the Montezuma County Historical Society and can be reached for comments or corrections at 882-2636.

We appreciate Frank sharing his family history for this article.

June Head is the historian for the Historical Society and can be reached for comments at 565-3880.